If there's one thing that can ruin a first date and ensure a woman's first impression of you is a bad one, it's crappy conversation.

You need ice breakers, light-hearted queries, questions that provoke banter, laughter, and thought, as well as questions that dig a bit deeper and go beyond the superficial. If she hates planes, road trips, or has no desire to leave her hometown ever, that's a good indicator of her ambitions and desires (or lackthereof).

Pick one thing on his profile and make fun of him for it.

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Better yet: "Many second date ideas can be born from this question." If you want the conversation to become a bit reflective, thoughtful, and meaningful, this is a great fall-back.

"Not only do you get to hear about her life story, but the snippet that's most meaningful and important to her," Jones explains.

Meet the experts: Sarah Jones is a relationship expert, and founder and CEO of coaching website Introverted Alpha, and Sameera Sullivan is the CEO of Lasting Connections, an elite matchmaking service. "This is a great ice-breaker because it's a little mischievous and flirtatious," Jones says.

"It's a sign you'd like to know her beyond surface level, while still giving her the freedom to reveal what she wants to share—and doesn't." This question lets you get a sense of what she feels strongly about and whether she's spirited and heartfelt.

) Using tiny pictures instead of words somehow makes asking someone out not so intimidating. Maybe it's because it shows that you don't take yourself too seriously and are maybe just a little bit kooky. Open with a random emoji (nail painting is always good) and wait.

You're also displaying your prowess with an i Phone and testing his ability to translate pictures into words. It's sort of like falling down as soon as you walk into a party: It's scary for a second, but breaks the ice so fast and so thoroughly that everyone can let their guard down.6. You may have heard every line in the book, but the average male has never had someone suggest that he fell from heaven. If he doesn't take the bait instantly and ask what's going on, follow up with "No?As a general rule, never do this, in any way, ever, til death. The reason is because you’ll come off like every other horn dog guy. Something that would have you eye-rolling, like, "Why is someone as hot as you looking for a date? " At this point, he's hooked — people cannot resist a mystery. " tell him it was a test that he failed, but he can make up for it by buying you a drink.8. Would You Rather or Fuck Marry Kill are fun ways to start a flirty conversation/suss out mutual enemies, and can almost always get a little dirty if you want them to.9."What's the best movie/book/meal you saw/read/ate in the past year?"You get a glimpse into her day, her job responsibilities, how she deals with stress, her energy level, tone, and how she spends her time," Jones says. Some say you never truly know someone until you travel with them.